Lithium hydroxide, monohydrate → HCID 68555610, compound

HRID 1501160Notes

Reaction equation

HRID 1501160 reaction equation
[O:1]([C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO.O>[O:1]([C:8]1[N:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89581068Ethyl 2-phenoxypyrimidine-5-carboxylate

Product 1

HCID 68555610HCID 68555610, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 2-phenoxypyrimidine-5-carboxylate (400 mg, 1.6 mmol) in mixed solution of tetrahydrofuran/methanol/water=3:1:1 (4 mL) was added lithium hydroxide monohydrate (200 mg, 8.4 mmol). The mixture was stirred at room temperature for 2 hours. The suspension was concentrated in vacuo. To the residue, was added water (50 mL) and extracted with dichloromethane (2*50 mL). The combined organic phase was separated, dried by sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5/1) to give the product 2-phenoxypyrimidine-5-carboxylic acid (300 mg, 79%) as pale solid.

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. additionTo the residue, was added water (50 mL)
  3. extractionextracted with dichloromethane (2*50 mL)
  4. customThe combined organic phase was separated
  5. dry with materialdried by sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue
  9. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-f7eb194fac094ea3b49d88b70e8da1a2
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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